Sodium Iodide → 3-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

HRID 1173834노트

반응식

HRID 1173834 반응식
[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]1=[O:19].Cl.Br[CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>>[ClH:1].[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([O:24][CH2:27][CH2:28][CH2:29][N:30]([CH3:32])[CH3:31])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:9]1=[O:19]

참가 물질

5

반응물 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 117103063-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-oneHCID 12440776(3-Bromo-propyl)-dimethyl-amine hydrochloride

생성물 1

HCID 117128103-[3-Chloro-6-(3-dimethylamino-propoxy)-benzo[b]thiophen-2-ylmethyl]-1-cyclohexyl-pyrrolidin-2-one hydrochloride salt

실험 절차

Using the procedure to synthesize Example 12 and using reagents 3-(3-chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one (150 mg, 0.412 mmol), (3-bromo-propyl)-dimethyl-amine hydrochloride (167 mg, 0.824 mmol), sodium iodide (62 mg, 0.412 mmol), and cesium carbonate (1.07 g, 3.30 mmol) afford the freebase of the title compound. Dissolve freebase in dichloromethane (5 mL) and add HCl in ether (2M, 0.4 mL), concentrate to give title compound (105 mg, 52%) as a yellow solid: Mass spectrum (apci) m/z=449.3 (M+H).

후처리

  1. customto synthesize Example 12

출처 및 근거

ORD 기록
ord-6dd880a8ec774983a6223b7864b974f6
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834194B2

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